1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents

Abstract

Compounds of the formulas ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl or hydroxy-lower-alkyl of 1-5 carbon atoms; R 1 and R 2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and R 8 is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when R 8 is hydrogen R' is hydroxy-lower-alkyl, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

We claim: 
     
       1. A compound of the formula ##STR24## wherein: Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl or hydroxy-lower-alkyl of 1-5 carbon atoms;   R 1  and R 2  are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and   R 8  is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when R 8  is hydrogen R' is hydroxy-lower-alkyl; or pharmaceutically acceptable acid-addition salts thereof.     
     
     
       2. A compound according to claim 1 of the formula ##STR25## wherein Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl of 1-5 carbon atoms; and R 1  and R 2  are hydrogen, halogen or lower-alkyl. 
     
     
       3. 5-{5-[2,6-Dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]pentyl}-3-methylisoxazole, according to claim 2. 
     
     
       4. 5-{3-[2,6-Dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]propyl}-3-methylisoxazole, according to claim 2. 
     
     
       5. 5-{3-[2,6-Dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]propyl}-3-ethylisoxazole, according to claim 2. 
     
     
       6. 5-{3-[2,6-Dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]propyl}-3-propylisoxazole, according to claim 2. 
     
     
       7. A compound according to claim 1 of the formula ##STR26## wherein Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl of 1-5 carbon atoms; and R 1  and R 2  are hydrogen, halogen or lower-alkyl. 
     
     
       8. 5-{5-[2,6-Dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentyl}-3-methylisoxazole, according to claim 7. 
     
     
       9. 5-{3-[2,6-Dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-3-methylisoxazole, according to claim 7. 
     
     
       10. 5-{3-[2,6-Dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-3-ethylisoxazole, according to claim 7. 
     
     
       11. A composition for combating picornaviruses which comprises an antivirally effective amount of a compound according to claim 1, in admixture with a suitable carrier or diluent. 
     
     
       12. A composition according to claim 11 for combating rhinoviruses.